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Cassandra Cummings creates a Safe Place for Black Women to Invest

Updated: Jul 30

Interview by Shanica Bell, Editor

Alexa, play Bia, Whole Lotta Money

“I think that we have been programmed as women, and particularly as black women, around different mindsets when it comes to money. And oftentimes, we’re told to go to school, get good grades, go get a great job, and work for a company for 30 plus years and then retire.” - Cassandra Cummings

Shanica Bell: So, we are just going to jump right in and chat about your brand, The Stocks & Stilettos Society. Needless to say, by the name alone, we’re going to talk about that bag. So go ahead and share who you are and what you do.

Cassandra: My name is Cassandra Cummings. I’m the founder of The Stocks & Stilettos Society. I say the fastest growing community of online women investors or online community of women investors. I like to call myself a financial cheerleader, I help women learn how to invest in the stock market in multiple ways: long term investing, as well as short term investing. So, I really, really like what I do.

Shanica Bell: How did you get into finance?

Cassandra: I got into finance by way of my dad. He was a man out in the community. And I kind of saw how he moved about, and I really wanted to be in a position where I could assist him with some business affairs. And so, for me, I needed to be rooted and have a very solid foundation of how money worked. And so that led me to wanting to major in finance, although I ended up changing to accounting. Then I had a mentor, a sharp black woman when I landed on the campus of USC who I was paired up with and she was a finance major. She was a bond trader at that time and I had never, ever seen a black woman as bad as she was in the world of finance. It encouraged me to keep going in this particular industry. So, yeah, it started with my dad, then she definitely gave me the push and the motivation to want to play on this playing field.

Shanica Bell: Awesome. So, how did you get your interest into stocks?

Cassandra: At 17, I actually lost my dad and I received the death benefit. It was a substantial amount of money for a 17-year-old so, with that death benefit came some financial advisors, and at 17, you know, you go from welfare to having this large sum of money, you really have to learn about money very quickly, very early on. So, it just piqued my interest to start to consume all of this information about investing, in the types of products that they were suggesting, and actually opening up accounts and putting more money in. I had to get an idea of how these sorts of accounts were being structured. So, at that age is when I got the first introduction into, ‘investing’. From there, I went on to finish school and try to learn more about the world of finance and the language of money and things like that because, I was fortunate to be able to receive money in a very bittersweet way from my dad. It also brought out people, I would say, a very interesting dynamic started to happen too, because these were people that I trusted, right? Yeah, I didn’t know who these people were. They just showed up with a check. And what ended up happening was they put me in high commission products, which I later found out and so it was really a catch 22, right? I was a little girl from the streets, grew up in the hood and now I have these ‘professionals’ helping me manage my money.

Shanica Bell: My condolences on that loss, that’s definitely got to be a hard situation. And then like you say, you’re 17 years old, your father’s past and you have this large sum of money. I think that it was very, very mature of you at that age, to even sit down and listen to those advisors. So, at what point did you get financially where you say, ‘okay, I think I got this, this is something that maybe I can package and teach to other people.’ How did that happen?

Cassandra: Well, I left Merrill & Lynch. At that point, I decided that I wanted to take on a different challenge. And that was a challenge of becoming self-employed. So, I actually went on to set up my own registered investment advisory firm and I was going to go out and actively recruit and pursue clients, but then I actually met someone on Periscope, who was in my own backyard. I went out to lunch with her and she told me that I needed to start a Facebook group. And I was like, what is that? Like, what does that look like? So, she kind of got me up, and told me this is what you do. I added her to the group. Before I knew it, the group started to really take off. It was a very interesting juxtaposition, if you will, because I had become accustomed to really like tracking people down and following up with people and asking, ‘hey, can I get an appointment? Let me help you roll over your 401k, let me help you set up your children’s college funds.’ And now I was in this Facebook group, where people were like, ‘help me, help me, help me!’ So that’s really how I got into teaching. But it’s very interesting, because I was a 7th grade math school teacher for Los Angeles Unified School District and I brought that experience with me, along with the experience of being a financial advisor. I basically found synergy in the Facebook group.

Shanica Bell: Wow. And so, from there, you started the group and now tell us about The Stocks & Stilettos Society and exactly what it is.

Cassandra: So, the Stocks & Stilettos Society is actually a community where we really have created a safe space for primarily black women to talk about money, I think that we have been programmed as women, and particularly as black women, around different mindsets when it comes to money. And oftentimes, we are told to go to school, get good grades, go get a great job, and work for a company for 30 plus years and then retire. So, what I wanted to do with the society is really give women an opportunity to feel empowered to feel like they can ask whatever questions they wanted to around money and not feel intimidated by those questions, and also see other sisters in there that are very, very confident when it comes to discussing money. It’s very collaborative environment. So, this society is a very unique sisterhood. I call it a financial sisterhood, if you will, where we really truly help each other, learn how money works, and help each other grow our money together.

Shanica Bell: So, let’s say a beginner comes to The Stocks & Stilettos Society. What would you recommend for a beginner who may have a lump sum of money? What free advice could you give?

Cassandra: I would say, you first have to take a course, and we have some classes in there that are free, that really kind of bring you up to speed on just becoming familiar with some of the terminology in the space. I think taking a class and better understanding some of the words and vernacular that’s used in the world of investing would be my advice. I think also, to really understanding what’s your goal? What’s your objective with investing the money? Is it investing for you to purchase your first home? Is it investing for you to retire early? Is it to pay off debt? Is it for you to take a vacation? That’s really going to determine how you set up your investments. And then, if you’re going to invest in or trade. Investing is going to be for the long term and trading is going to be short term. So, we offer support, and we offer courses in both of those areas.

Shanica Bell: Some people don’t believe that the way they think or feel about money directly affects their pockets in a good way or a bad way. Tell us how a shift in a person’s mindset about money can take them from rags to riches, elaborate on that for me.

Cassandra: I think a mindset shift is very important. Because oftentimes women don’t feel like they’re deserving of having their own money and making their own decisions around money. I think like 85% of women at some point will have to control their own money, whether they’re married or not. At some point, they have to become familiar with managing money. And so, a mindset shift is so important, but you also have to get around the right people to make that transition. Because even though your thoughts directly affect how you invest and how you move with money, the people around you indirectly affect how you invest and how you move with money as well. So, if you’re around three broke friends, guess what? You probably won’t end up broke, if you’re around three rich friends. More than likely, you’re going to end up being rich, too. So, mindset is huge. Being around people that you aspire to be like that speaks volumes about being able to make a mind shift around money.

Shanica Bell: So how would a person who lives paycheck to paycheck get started in the smallest way into investing?

Cassandra: If you’re living paycheck to paycheck, the best way would be one of the micro investing apps such as Acorns or Stash App, it gives you an opportunity to kind of get in on the ground floor. Always see stocks as self-care at some point, once you build up enough in some of these micro investing apps, a few $1,000, then it’s time to really graduate, if you will, to some of the more beginning platforms such as Robin Hood, E-trade or Stockpile where you can select your individual stocks or get access to broader ETFs exchange traded funds.

Shanica Bell: Miss Cassandra, there’s not enough for black women to be educated in topics like this. And I commend you for taking that mantle and doing that. How can our readers connect?

Cassandra: Feel free to follow us and join our community at the Stocks & Stilettos Society on Facebook, you can follow us on Instagram. And we hope that you can become a Stock Sistar!

Learn more about The Stocks & Stilettos Summit - October 2022 and Queens Capital retreats and events by visiting Be sure to follow the group on Facebook.


To hear this interview in its entirety, check out ‘The Brand Cafe’ with host Shanica LaShay, Editor of Life in the Overflow Magazine,

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